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Ethynylene-bridged acenes, which are pi-conjugated triple bond-containing systems, have attracted increasing interest as promising organic semiconductor materials due to their delocalized pi-electrons. In this study, ethynylene-bridged pentacene precursor oligomers were not only synthesized through multiple-organic reactions but also were unexpectedly obtained in one-pot by using a conventional reaction with lithium silylacetylide and quinone. In the case of one-pot synthesis, the formation of oligomers, including pentamer, was evidently confirmed by matrix-assisted-laser-desorption/ionization time-of-flight mass spectrometry. Single crystal X-ray analysis visualized the ethynylene-bridged structure of the dimer which was one of the major products in the one-pot reaction. It was found that the reaction time for the lithiation was the key factor in controlling oligomer formation. Finally, the thermal conversion from pentacene precursors to the corresponding pentacene oligomers was achieved via retro-Diels–Alder reaction. These results would open an access to synthesize a wide range of pi-conjugated systems.

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  This is the peer reviewed version of the following article: Ethynylene-Bridged Pentacene Trimer and Tetramer Prepared Through Unexpected Oligomerization and Their Subsequent Thermal Conversions, which has been published in final form at https://doi.org/10.1002/ejoc.202400770. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

Keyword: pentacene, oligomer, thermal conversion, single crystal, precursor approach

Date published: 2024-12-09

Publisher: Wiley-Blackwell

Journal:

• EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (ISSN: 10990690) e202400770

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Manuscript type: Author's version (Accepted manuscript)

MDR DOI: https://doi.org/10.48505/nims.5063

First published URL: https://doi.org/10.1002/ejoc.202400770

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Updated at: 2025-08-13 08:30:36 +0900

Published on MDR: 2025-08-13 08:17:13 +0900